1-Butanol → HCID 59825715, compound

Participants

Reaction Steps

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.095 g, 0.62 mmol), 5-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-ylsulfanyl)-furan-2-carbaldehyde (0.20 g, 0.62 mmol) and 1,3-cyclohexanedione (0.069 g, 0.62 mmol) in 10 ml of 1-butanol is heated at reflux temperature for 4 h. The reaction mixture is then concentrated under reduced pressure and the residue is purified on a silica gel column (34 g) eluted with a mixture of cyclohexane and ethyl acetate (7/3, v/v). The fractions containing the expected product are concentrated under reduced pressure. The residue is resuspended in 2 ml of acetonitrile, heated at reflux temperature for 30 minutes and let to cool to room temperature. The insoluble material is collected by filtration and dried under vacuum to yield 19 mg of 9-[5-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester. Yield=6%. Analytical LC/MS (method B): m/z=555 (positive ion mode [M+H]+), m/z=553 (negative ion mode [M−H]−).

Provenance & Evidence